cas 387-46-2, 2,6-Dihydroxybenzaldehyde | Articles data

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Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones
A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.
Huang, Xihua,Liu, Jie,Sheng, Jianfei,Song, Xianheng,Du, Zhibo,Li, Mingkang,Zhang, Xuejing,Zou, Yong
supporting information
p. 804 - 808
(2018/03/06)

2,6-Dihydroxybenzaldehyde Analogues of the Iron Chelator Salicylaldehyde Isonicotinoyl Hydrazone: Increased Hydrolytic Stability and Cytoprotective Activity against Oxidative Stress
Salicylaldehyde isonicotinoyl hydrazone (SIH) is a small molecule and lipophilic chelating agent that firmly binds ferric ions from the cellular labile iron pool and is able to protect various tissues against oxidative damage. Previously, SIH possessed the best ratio of cytoprotective efficiency to toxicity among various iron chelators, including the desferrioxamine, deferiprone, and deferasirox used in clinical practice. Here, we prepared a series of 2,6-dihydroxybenzaldehyde aroylhydrazones as SIH analogues with an additional hydroxyl group that can be involved in the chelation of metal ions. Compound JK-31 (2,6-dihydroxybenzaldehyde 4-chlorobenzohydrazone) showed the best cytoprotective efficiency among the studied compounds including SIH. This compound significantly protected H9c2 cardiomyoblast cells against oxidative stress induced by various pro-oxidants, such as hydrogen peroxide, tert-butyl hydroperoxide, paraquat, epinephrine, N-acetyl-p-benzoquinone imine (a toxic metabolite of paracetamol), and 6-hydroxydopamine. The exceptional cytoprotective activity of JK-31 was confirmed using epifluorescence microscopy, where JK-31-treated H9c2 cells maintained a higher mitochondrial inner membrane potential in the presence of a lethal dose of hydrogen peroxide than was observed with cells treated with SIH. Hence, this study demonstrates the deleterious role of free iron ions in oxidative injury and the potential of 2,6-dihydroxybenzaldehyde aroylhydrazones in the prevention of various types of cardiac injuries, highlighting the need for further investigations into these compounds.
Jansová, Hana,Kube?, Jan,Reimerová, Petra,?těrbová-Kova?íková, Petra,Roh, Jaroslav,?imunek, Tomá?
p. 1151 - 1163
(2018/11/23)

PROCESS FOR SYNTHESIZING 2-HYDROXY-6-((2-(1-ISOPROPYL-1H-PYRAZOL-5-YL)-PYRIDIN-3-YL)METHOXY)BENZALDEHYDE
Disclosed herein are processes for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1H- pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde (also referred to herein as Compound (I)) and intermediates used in such processes. Compound (I) binds to hemoglobin and increases it oxygen affinity and hence can be useful for the treatment of diseases such as sickle cell disease.
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(2017/12/01)

Discovery and Rational Design of Natural-Product-Derived 2-Phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine Analogs as Novel and Potent Dipeptidyl Peptidase 4 (DPP-4) Inhibitors for the Treatment of Type 2 Diabetes
Starting from the lead isodaphnetin, a natural product inhibitor of DPP-4 discovered through a target fishing docking based approach, a series of novel 2-phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine derivatives as potent DPP-4 inhibitors are rationally designed utilizing highly efficient 3D molecular similarity based scaffold hopping as well as electrostatic complementary methods. Those ingenious drug design strategies bring us approximate 7400-fold boost in potency. Compounds 22a and 24a are the most potent ones (IC50 ≈ 2.0 nM) with good pharmacokinetic profiles. Compound 22a demonstrated stable pharmacological effect. A 3 mg/kg oral dose provided >80% inhibition of DPP-4 activity within 24 h, which is comparable to the performance of the long-acting control omarigliptin. Moreover, the efficacy of 22a in improving the glucose tolerance is also comparable with omarigliptin. In this study, not only promising DPP-4 inhibitors as long acting antidiabetic that are clinically on demand are identified, but the target fish docking and medicinal chemistry strategies were successfully implemented.
Li, Shiliang,Xu, Hongling,Cui, Shichao,Wu, Fangshu,Zhang, Youli,Su, Mingbo,Gong, Yinghui,Qiu, Shaobing,Jiao, Qian,Qin, Chun,Shan, Jiwei,Zhang, Ming,Wang, Jiawei,Yin, Qiao,Xu, Minghao,Liu, Xiaofeng,Wang, Rui,Zhu, Lili,Li, Jia,Xu, Yufang,Jiang, Hualiang,Zhao, Zhenjiang,Li, Jingya,Li, Honglin
p. 6772 - 6790
(2016/08/05)

Benzo-hexatomic ring derivative used as DPP-4 inhibitor and application of benzo-hexatomic ring derivative
The invention relates to a benzo-hexatomic ring derivative used as a DPP-4 inhibitor and application of the benzo-hexatomic ring derivative, in particular to compounds shown as in formula I, medicine compositions with the compounds shown as in the formula I and application of the compounds in preparing medicines for treating diseases related to DPP-4 or inhibiting the DPP-4.
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Paragraph 0130; 0134; 0135; 0136

(2016/10/09)

ALDEHYDE COMPOUNDS FOR TREATING PULMONARY FIBROSIS, HYPOXIA, AND CONNECTIVE TISSUE AND AUTOIMMUNE DISEASE
This disclosure relates to use of certain aldehyde compounds for treating pulmonary fibrosis, hypoxia, and connective tissue and autoimmune disease such as scleroderma, lupus, arthritis and related conditions in a mammal.
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Page/Page column 26

(2016/10/27)

Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N?H Acidity of the Distal Base
The distal hydrogen bond (H-bond) in dioxygen-binding proteins is crucial for the discrimination of O2with respect to CO or NO. We report the preparation and characterization of a series of ZnIIporphyrins, with one of three meso-phenyl rings bearing both an alkyl-tethered proximal imidazole ligand and a heterocyclic distal H-bond donor connected by a rigid acetylene spacer. Previously, we had validated the corresponding CoIIcomplexes as synthetic model systems for dioxygen-binding heme proteins and demonstrated the structural requirements for proper distal H-bonding to CoII-bound dioxygen. Here, we systematically vary the H-bond donor ability of the distal heterocycles, as predicted based on pKavalues. The H-bond in the dioxygen adducts of the CoIIporphyrins was directly measured by Q-band Davies-ENDOR spectroscopy. It was shown that the strength of the hyperfine coupling between the dioxygen radical and the distal H-atom increases with enhanced acidity of the H-bond donor.
Alberti, Mariza N.,Polyhach, Yevhen,Tzirakis, Manolis D.,T?dtli, Laura,Jeschke, Gunnar,Diederich, Fran?ois
supporting information
p. 10194 - 10202
(2016/07/19)

Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes Dedicated to Prof. Véronique Gouverneur on the occasion of her receipt of the 2014 ACS Award for Creative Work in Fluorine Chemistry.
Treatment with a cationic palladium(II) catalyst promoted the Friedel-Crafts-type cyclization of 1,1-difluoro-1-alkenes bearing a biphenyl skeleton to afford regioselectively fluorinated (pinpoint-fluorinated) phenanthrenes via C-F bond activation. The obtained pinpoint-fluorinated phenanthrenes were observed to be organized by π-π and C-H?F interactions to exhibit columnar and layer structures in the solid state.
Fuchibe, Kohei,Morikawa, Toshiyuki,Ueda, Ryu,Okauchi, Tatsuo,Ichikawa, Junji
supporting information
p. 106 - 115
(2015/11/10)

The flavan-isoflavan rearrangement: Bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence
An approach to 2-substituted isoflavonoids is reported based on the 1,2-shift of the aryl group in the catechin skeleton followed by the in situ alkylation. Synthesis of (-)-equol, a natural isoflavan with estrogenic activities, was achieved.
Nakamura, Kayo,Ohmori, Ken,Suzuki, Keisuke
supporting information
p. 7012 - 7014
(2015/04/22)

Compounds and uses thereof for the modulation of hemoglobin
Provide herein are compounds and pharmaceutical compositions suitable as modulators of hemoglobin, methods and intermediates for their preparation, and methods for their use in treating disorders mediated by hemoglobin and disorders that would benefit from tissue and/or cellular oxygenation.
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Paragraph 0274-0275

(2014/09/29)

Towards a library of chromene cannabinoids: A combinatorial approach on solid supports
A novel solid-phase synthesis towards classical cannabinoids is presented. Starting from immobilized salicylaldehydes the desired THC-analogous tricycles are obtained in four atom-economic steps including cleavage. The reagents of the employed reactions (domino oxa-Michael-aldol, Wittig, and Diels-Alder) can be varied easily, providing the basis for a combinatorial approach. Overall yields range from 20-60%. Georg Thieme Verlag Stuttgart New York.
Kapeller, Dagmar C.,Br?se, Stefan
supporting information; experimental part
p. 161 - 164
(2011/03/19)

Design, synthesis, and biological evaluation of coumarin derivatives tethered to an edrophonium-like fragment as highly potent and selective dual binding site acetylcholinesterase inhibitors
A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The highest AChE inhibitory potency in the 3-hydroxy-N,N-dimethylanilino series was observed with a 6,7-dimethoxy-3-substituted coumarin derivative, which, along with an outstanding affinity (IC50=0.236 nm) exhibits excellent AChE/BChE selectivity (SI>300 000). Most of the synthesized 3-hydroxy-N,N,N- trialkylbenzaminium salts display an AChE affinity in the sub-nanomolar to picomolar range along with excellent AChE/BChE selectivities (SI values up to 138 333). The combined use of docking and molecular dynamics simulations permitted us to shed light on the observed structure-affinity and structure-selectivity relationships, to detect two possible alternative binding modes, and to assess the critical role of π-π stacking interactions in the AChE peripheral binding site.
Pisani, Leonardo,Catto, Marco,Giangreco, Ilenia,Leonetti, Francesco,Nicolotti, Orazio,Stefanachi, Angela,Cellamare, Saverio,Carotti, Angelo
experimental part
p. 1616 - 1630
(2011/11/29)

Probing hydrogen bonding to bound dioxygen in synthetic models for heme proteins: The importance of precise geometry
Distal hydrogen bonding in natural dioxygen binding proteins is crucial for the discrimination between different potential ligands such as O2 or CO. In the present study, we probe the chemical requirements for proper distal hydrogen bonding in a series of synthetic model compounds for dioxygen-binding heme proteins. The model compounds 1-Co to 7-Co bear different distal residues. The hydrogen bonding in their corresponding dioxygen adducts is directly measured by pulse EPR spectroscopy. The geometrical requirements for this interaction to take place were found to be narrow and very specific. Only two model complexes, 1-Co and 7-Co, form a hydrogen bond to bound dioxygen, which was characterized in terms of geometry and nature of the bond. The geometry and dipolar nature of this interaction in 1-Co-O2 is more similar to the one in natural cobalt myoglobin (Co-Mb), making 1-Co the best model compound in the entire series.
Dube, Henry,Kasumaj, Besnik,Calle, Carlos,Felber, Beatrice,Saito, Makoto,Jeschke, Gunnar,Diederich, Francois
supporting information; experimental part
p. 125 - 135
(2009/07/09)

Efficient and selective reduction protocols of the 2,2-dimethyl-1,3- benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols
Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl-1,3-benzodioxan-4- one functional group with DIBAL-H or LAH, respectively.
Bajwa, Naval,Jennings, Michael P.
p. 3646 - 3649
(2007/10/03)

Synthesis of dendritic metalloporphyrins with distal H-bond donors as model systems for hemoglobin
We report the synthesis of the first- (G1) and second-generation (G2) dendritic FeII porphyrins 1-Fe-4-Fe (G1) and 6 · Fe (G2) bearing distal H-bond donors ideally positioned for stabilization of Fe II-O2 adducts by H-bonding (Fig. 1). A first approach towards the construction of these novel biomimetic systems failed unexpectedly: the Suzuki cross-coupling between appropriately functionalized ZnII porphyrins and orthoethynylated aryl derivatives, serving as anchors for the distal H-bond donor moieties, was unsuccessful (Schemes 1, 3, and 5), presumably due to steric hindrance resulting from unfavorable coordination of the ethynyl residue to the Pd species in the catalytic cycle (Scheme 6). The target molecules were finally prepared by a route in which the ortho-ethynylated meso-aryl ring is introduced during porphyrin construction in a mixed condensation involving the two dipyrrylmethanes 33 and 34, and aldehyde 36 (Schemes 7 and 8). Following attachment of the dendrons (Scheme 11), the distal H-bond donors were introduced by Sonogashira cross-coupling (Scheme 12), and subsequent metallation afforded the dendritic FeII porphyrins 1 · Fe-6 · Fe. 1H-NMR Spectroscopy proved the location of the H-bond donor moiety atop the porphyrin surface, and X-ray crystal-structure analysis of model system 45 (Fig. 2} revealed that this moiety would not sterically interfere with gas binding. With 1,2-dimethyl-1H-imidazole (DiMeIm) as ligand, the dendritic FeII porphyrins formed five-coordinate high-spin complexes (Figs. 3 and 4) and addition of CO led reversibly to the corresponding stable six-coordinate gas complexes (Fig. 6). Oxygenation, however, did not result in defined FeII-O2 complexes as rapid decomposition to FeIII species took place immediately, even in the case of the G2 dendrimer 6·Fe(DiMeIm) (Fig. 7). In contrast, stable gas adducts are formed between dendritic CoII porphyrins and O 2 in the presence of DiMeIm as axial ligand, as revealed by electron paramagnetic resonance (EPR). The possible stabilization of these complexes through H-bonding involving the distal ligand is currently under investigation in multidimensional and multifrequency pulse EPR experiments.
Felber, Beatrice,Diederich, Francois
p. 120 - 153
(2007/10/03)

Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1
Potent and selective Candida albicans N-myristoyltransferase (CaNmt) inhibitors have been identified through optimization of a lead compound 1 discovered by random screening. The inhibitor design is based on the crystal structure of the CaNmt complex with compound (S)-3 and structure-activity relationships (SARs) have been clarified. Modification of the C-4 side chain of 1 has led to the discovery of a potent and selective CaNmt inhibitor 11 (RO-09-4609), which exhibits antifungal activity against C. albicans in vitro.
Masubuchi, Miyako,Kawasaki, Ken-ichi,Ebiike, Hirosato,Ikeda, Yoshihiko,Tsujii, Shinji,Sogabe, Satoshi,Fujii, Toshihiko,Sakata, Kiyoaki,Shiratori, Yasuhiko,Aoki, Yuko,Ohtsuka, Tatsuo,Shimma, Nobuo
p. 1833 - 1837
(2007/10/03)

MEDICAL USE OF ORGANIC AEROGELS AND BIODEGRADABLE ORGANIC AEROGELS
Physiologically acceptable organic aerogels, including pyrolysed aerogels, for use in medicine, for example as diagnostic agents, artificial tissues, organs and organ components etc., and in particular in drug delivery systems. Use of biodegradable organic aerogels, which are themselves novel materials, is preferred e.g. for materials such as diagnostic and therapeutic agents for parenteral administration.
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(2008/06/13)

Regioselective synthesis of 6-substituted 2-hydroxybenzaldehyde: Efficient synthesis of the immunomodulator tucaresol and related analogues
Two new improved procedures have been developed for the preparation of the immunostimulant tucaresol 1 [4-(2-formyl-3-hydroxyphenoxymethyl)benzoic acid]. These approaches, which start from resorcinol or 2,6-dimethoxybenzaldehyde, are practical and therefore amenable to scale-up. In the case of the second approach, the multi-step synthesis reported in the literature has been reduced to three steps. Furthermore, unlike the reported method, our synthesis is versatile for the preparation of tucaresol analogues. The method is general and applicable for the preparation of 6-substituted 2-hydroxybenzaldehydes.
Zacharie, Boulos,Attardo, Giorgio,Barriault, Nancy,Penney, Christopher
p. 2925 - 2929
(2007/10/03)

Synthesis of porphyrins tailored with eight facially-encumbering groups. An approach to solid-state light-harvesting complexes
Synthetic models of the photosynthetic antenna complexes must achieve long-range 3-dimensional order encompassing a large number of porphyrinic pigments with limited direct contact of the pigments. In order to develop solid-state antenna complexes, we have synthesized porphyrins bearing benzyloxy groups projecting over both faces and optionally also around the periphery of the porphyrin. Routes have been established for prefunctionalizing benzaldehydes with various benzyloxy groups. Reaction of 2,6-bis, 3,5-bis, or 2,4,6-tris(benzyloxy)benzaldehydes with pyrrole via the room temperature two-step one-flask porphyrin reaction provides direct access to the facially-encumbered porphyrins. The benzyloxybenzaldehydes react as efficiently as methoxybenzaldehydes, indicating the utility of the -OCH2- unit for introducing large substituents near the face of the porphyrin. The octakis and dodecakis(benzyloxy)porphyrins exhibit characteristic porphyrin absorption and fluorescence properties in solution. The crystal structure of meso-tetrakis[2,6-bis(2,3,4,5,6-pentalfuorobenzyloxy)phenyl]porphyrin has been determined. The pentafluorobenzyloxy substituents provide a cavity on each side of the porphyrin plane which has an approximate cylindrical shape with a diameter of ~7.5 A and a height of ≥4.5 A. The porphyrin core parameters are those obtained for free base derivatives in which the inner hydrogen atoms are ordered. Crystal data: a=14.759 (1) A, b=25.519 (2) A, c=13.100 (1) A, α=100.04 (1), β=99.83 (1), γ=88.25 (1), V=4767.3 (6) A3, all measurements at 127 K, triclinic, space group P1, Z=2 R1(F)=0.097, for 10020 'observed' data, and wR2(F2)=0.275 for 17761 total unique (all) data.
Wagner,Wagner, Richard W.,Lindsey,Lindsey, Jonathan S.,Turowska-Tyrk,Turowska-Tyrk, Ilona,Scheidt,Scheidt, W. Robert
p. 11097 - 11112
(2007/10/02)

A Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent (I): A Synthesis of Methoxy- and Hydroxycoumarins
Reaction of methoxy- and hydroxysalicylaldehydes (1) with phosphorane in diethylaniline under reflux gave only coumarins (3) in high yields except for 3-methoxysalicylaldehyde (1b).It was clarified that methoxy group(s) at C4 and C6 on 1 facilitated the formation of 3.
Harayama, Takashi,Katsuno, Keiko,Nishioka, Hiromi,Fujii, Masako,Nishita, Yoshitaka,et al.
p. 613 - 622
(2007/10/02)

Selective Syntheses Using Cyclodextrin as Catalyst. 1. Control of Orientation in the Attack of Dichlorocarbene at Phenolates
4-Hydroxybenzaldehydes, 2,4-dihydroxybenzaldehyde, and 4-(dichloromethyl)-2,5-cyclohexadienones were synthesized in virtually 100percent selectivities and high yields from the corresponding phenols and chloroform in alkaline aqueous solutions by using α- or β-cyclodextrin (α- or β-CD) as catalyst.The regulation of the molar ratio of chloroform to CD below unity throughout the reaction time, by controlling the rate of addition of chloroform, was definitely required to attain high selectivity.Under these conditions, dichlorocarbene, prepared in situ from chloroform and sodium hydroxide, attacked overwhelmingly at the para carbon of phenols with almost perfect suppression of the reaction at the ortho carbon.The structure of the ternary molecular complex composed of β-CD, chloroform, and phenol, formed in the reaction mixture for the selective synthesis of 4-hydroxybenzaldehyde, was determined by NMR spectroscopy.The selective catalysis by CDs was attributed to the regulation of molecular conformation of phenols with respect to chloroform, and thus to dichlorocarbene, in the ternary complex.
Komiyama, Makoto,Hirai, Hidefumi
p. 2018 - 2021
(2007/10/02)

Process of preparing hexahydropyrimidines
This invention relates to hexahydropyrimidines (HHP) of the formula STR1 where R' is a substituted group and R is hydrogen or a substituted group; the process of preparing and the uses therefor, particularly as deterioration inhibitors in hydrocarbon fuels.
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(2008/06/13)